New England’s Great Barrington for Pumpkins


For our annual pumpkin and apple festivities this year, we headed to Great Barrington, Massachusetts, which is about a three hour drive from New York City.

To Eat

We had a delicious meal at farm-to-table restaurant Prairie Whale. It was started by an ex-Brooklynite, and definitely has that hip, rustic vibe. The cornbread with jalapeno butter was a huge hit, as was the Cerdon sparkling rose (honestly, it was probably the best rose I’ve ever taste–reminded me of forest fruit from Sweden, complete with millions of tiny bubbles! I found it locally here in NYC at Astor Wines, if you want to give it a try!)

And, ever the fans of the Red Lion Inn, we went there for a delightful lunch, filled with warm soups, cheese plates, and Oktoberfest ales! The place is super cozy and basically screams fall with the giant pumpkins out front and fire roaring in the lobby.

To Do

Wanting to experience foliage, we were torn between a “gentle hike” up the mountain or a (much) gentler stroll around the Berkshire Botanical Garden…in the end we went with much gentler:-) And so very happy we did! The garden was small as gardens go (much smaller than the one in the Bronx, for comparison), but truly beautiful and curated. And the children’s garden was a true delight! There were stumps for jumping, pails for watering, shovels for digging, pumpkins for picking, and even a fairy garden for exploring! Augusten could have easily stayed the entire day.

We also spent time exploring the towns of Stockbridge and Great Barrington, popping into tiny shops filled with records, used books, locally made soaps, jewelry, crystals and stones, and tons of coffee.
Two that really stood out this time around were Rubiner’s for their fantastic selection of cheese and wine (pick some up for a cozy dinner back at the hotel!) and One Mercantile, for their yummy pumpkin scented candles, locally handmade greeting cards, and unique (and reasonably priced!) jewelry.

To Stay

We stayed at the Briarcliff Motel again, and again, were so pleased. The bonfire out front was so lovely to sit around in the evenings, and the hammocks out back were wonderful for mid-afternoon rests.

The rooms are all decked out in quirky 1960’s decor, and at a little over $100 a night, you just can’t go wrong. Oh! And, they paired up with the swanky Red Lion Inn right down the road, and you can now go and use their gym and outdoor heated pool, free of charge. A nice little perk!


Jessica Tiare Bowen
Jessica Tiare Bowen lives in the juicy Big Apple with her adorable pink-nosed chihuahua, Gillman. He's the inspiration for her first published children's book, "Park Avenue Pound Puppy." The book is the combined result of her two greatest passions: pooches and penning stories.

Her passions include art, urban hikes through Manhattan, drinking coffee with 3 creams and 6 sugars, making extremely detailed itineraries and traveling to far away places, singing along to Broadway shows, Netflix movie nights, discovering incredible treasures at Goodwill and thrift stores, and listening to stories from little people under 7 and big people over 70.

She started her career as New York City Teaching Fellow, teaching elementary school and theater arts at a special education school in the South Bronx for 6 years. She is now a Special Education School Improvement Specialist working in public schools throughout New York City. She is the Editor-In-Chief of the online New York City travel magazine, Used York City. The magazine focuses on finding the best of New used by New Yorkers. She is a member of the Society of Children's Book Writers and Illustrators, and an ASPCA Ambassador.
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